O-Phenylenediamine → HCID 22141121, compound

HRID 428954Notes

Reaction equation

HRID 428954 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:15]=[C:16]([C:20](=[NH:24])OCC)[CH:17]=[CH:18][CH:19]=2)[CH3:13])[C:8]1=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1N>CO>[NH:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[N:26]=[C:20]1[C:16]1[CH:15]=[C:14]([C:10]2([CH3:13])[CH:9]3[CH:11]2[CH2:12][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]3=[O:25])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 22141159HCID 22141159, compound

Product 1

HCID 22141121HCID 22141121, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl 3-(3-hexyl-6-methyl-2-oxo-3-azabicyclo[3.1.0]hex-6-yl)benzenecarboximidoate (Preparation 42, 0.13 g, 0.34 mmol) in methanol (4 ml) at room temperature was added 1,2-diaminobenzene (37 mg, 0.34 mmol) and the mixture was heated under reflux for 1 h and then cooled and concentrated in vacuo. The residue was dissolved in dichloromethane (10 ml) and washed with 10% aqueous potassium carbonate solution (10 ml). The aqueous layer was then reextracted with dichloromethane (2×8 ml). The combined organic layers were dried (MgSO4) and then concentrated in vacuo. The crude residue was purified by chromatography on silica gel eluting with hexane:ethyl acetate (1:1 and then 1:2) to give the title compound as a white foam (61 mg, 47%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  6. washwashed with 10% aqueous potassium carbonate solution (10 ml)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by chromatography on silica gel eluting with hexane:ethyl acetate (1:1

Sources & evidence

ORD record
ord-4dd4c2bbcfe642ac92b9a6806da8ca00
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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